Bridgeport Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Bridgeport Vacation Homes

Cozy 2 bedroom home located minutes from downtown
Kitchen features a central island, microwave, coffee maker, and dining table with four chairs.

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown
Stareway to Heaven Su
Relax on the covered outdoor deck with a sofa and enjoy the view.

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
Stareway to Heaven Su
Beautiful historic home in Stony Brook!
Enjoy meals in this kitchen with a dining table, sink, and refrigerator.

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!
Cozy 3 bedroom minutes from Yale and the beach
Kitchen features a central island, oven, and white cabinetry with a patterned backsplash.

Cozy 3 bedroom minutes from Yale and the beach

7.0 out of 10, Good, (2)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the outside.

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (4)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Business or Weekend escape
Enjoy a refreshing swim under the stars at our pool, surrounded by a spacious deck.

Business or Weekend escape

9.2 out of 10, Wonderful, (44)
"Very nice owner with great communication. "
The price is CA $117
CA $201 total
includes taxes & fees
Aug 13 - Aug 14
Business or Weekend escape
Minutes to Walnut Beach, newly renovated 3 bedroom home
Enjoy a serene beachside retreat with a balcony overlooking the tranquil ocean.

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (6)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Enjoy the serene ocean views from the comfort of your beachside retreat.

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (121)
"Beautiful historic home, views of the Sound, pleasant walking neighborhood."
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Stay at Black Rock Harbor
A two-story house with a central entrance and dormer windows above.

Stay at Black Rock Harbor

10.0 out of 10, Exceptional, (21)
"Lovely home, responsive host & convenient location with water views. Cute & comfy decor with well appointed kitchen and off street parking. "
Stay at Black Rock Harbor
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Traditional home with a charming front porch and beautifully landscaped yard.

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is CA $478
CA $946 total
includes taxes & fees
Sep 3 - Sep 4
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Soothing Carriage House with Hot Tub in charming Stratford
Interior

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (1)
"John was a wonderful Host.We had a very relaxing time in the Hot Tub and the carriage house had everything we needed for our stay.We will definitely book again,Lisa and Holly"
Soothing Carriage House with Hot Tub in charming Stratford
Cheerful 4 bedrooms residential house.
Traditional home with a charming front porch and white picket fence, surrounded by beautiful flowering plants.

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (31)
"House was perfect for what we needed. Great proximity to the Amphitheater and Seaside Park. "
Cheerful 4 bedrooms residential house.
Beach Bungalow, walk to beach, private backyard
Fridge, microwave, oven, dishwasher

Beach Bungalow, walk to beach, private backyard

10.0 out of 10, Exceptional, (3)
"The property was perfect for all of us. It was in a quiet neighborhood and great location."
Beach Bungalow, walk to beach, private backyard
Lakeside luxury: beautiful, relaxing 4 bedroom home
Relax in a serene lakeside setting with a picturesque tree providing shade and a tranquil atmosphere.

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (27)
"This property was perfect for our needs! Checking in and out was simple and easy. The house is spacious and backyard is gorgeous! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Charming 2-bedroom house with WiFi, AC in Fairfield
Relax in a stylish living space with a geometric sculpture, potted plant, and modern sofa.

Charming 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (3)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is CA $204
CA $474 total
includes taxes & fees
Aug 19 - Aug 20
Charming 2-bedroom house with WiFi, AC in Fairfield
Blue Cottage East Setauket
Fridge, microwave, oven, stovetop

Blue Cottage East Setauket

Blue Cottage East Setauket
Charming 3 Bedroom Beach Front Cottage with Fireplace
Kitchen area with a granite countertop, black microwave, stainless steel stove, and dishwasher.

Charming 3 Bedroom Beach Front Cottage with Fireplace

9.4 out of 10, Exceptional, (28)
"Beautiful view / location"
Charming 3 Bedroom Beach Front Cottage with Fireplace
Family Gem on Dyer Street
Dining

Family Gem on Dyer Street

The price is CA $562
CA $1,249 total
includes taxes & fees
Aug 11 - Aug 12
Family Gem on Dyer Street
The Jewel of The Cove - Historic Coastal Retreat
Enjoy a serene beach experience with sailboats on the calm sea and palm trees along the shoreline.

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (4)
"loved it so much, beautiful property 100 % would stay again "
The price is CA $284
CA $703 total
includes taxes & fees
Aug 17 - Aug 18
The Jewel of The Cove - Historic Coastal Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bridgeport Hotel Reviews

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
"This is my Go-To / First Choice when visiting the Fairfield area. Rooms are always clean & immaculate + very comfy bed, great towels, good size room...and traveling alone I feel safe! Staff is so welcoming and extra helpful. Keep it up."
Nancy 2-night trip
Posted 14 hours ago
The Circle Hotel Fairfield